GB989144A - Polyether polyols and polyurethane foams derived therefrom - Google Patents
Polyether polyols and polyurethane foams derived therefromInfo
- Publication number
- GB989144A GB989144A GB2781963A GB2781963A GB989144A GB 989144 A GB989144 A GB 989144A GB 2781963 A GB2781963 A GB 2781963A GB 2781963 A GB2781963 A GB 2781963A GB 989144 A GB989144 A GB 989144A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diisocyanate
- specified
- glycol
- anhydrohexitols
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/487—Polyethers containing cyclic groups
- C08G18/4883—Polyethers containing cyclic groups containing cyclic groups having at least one oxygen atom in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention comprises polyoxypropylene anhydrohexitols of hydroxyl number 350-750 containing no more than 10 mol. per cent polyoxypropylene glycol. The compounds may be prepared by reacting propylene oxide with an anhydrohexitol at 90-150 DEG C. in the absence of water and in the presence of a basic catalyst. Sufficient propylene oxide may be added to form chains 2-10 units long on some or all of the hydroxyl groups. Anhydrohexitols specified are 1,4-, 1,5-, 2,6-, and 3,5- anhydrosorbitol and anhydromannitol and 1,4: 3,6-dianhydrosorbitol or mixtures thereof. They may be obtained by reducing the corresponding hexose. 0.01-0.5 molecules of catalyst may be used per hydroxy group. Catalysts specified are the hydroxides, methoxides and ethoxides of sodium and potassium and the alkali metal alcoholates of the anhydrohexitols. The reaction may be carried out under a nitrogen atmosphere and at elevated pressure. A solvent may be employed, e.g. dimethyl formamide, dimethyl sulphoxide, a hydrocarbon, ether or heterocyclic base. A basic solvent may also function as a catalyst. In examples (3-6) the product is purified by dilution with water and passage down a cation-exchange resin column.ALSO:A polyurethane foam may be produced by adding a polyisocyanate and a blowing agent to a polyol of OH number 350-750 prepared by interacting an anhydro-hexitol and propylene oxide at 90-150 DEG C., in the presence of a basic catalyst and in the absence of water. Anhydrohexitols specified are 1,4-, 1,5-, 2,5- and 3,6- anhydrosorbitol, 1,4-, 1,5-, 2,6- and 3,6- anhydromannitol, 1,4,3,6 - di - anhydrosorbitol and dianyhydromannitol. Mixtures of isomers may be used. Catalysts specified are the hydroxides, methoxides and ethoxides of sodium and potassium and the alkali metal alcoholates of the anhydrohexitols. 0.01-0.5 equivalents may be used per equivalent of hydroxyl group. The propylene oxide addition reaction may be carried out at atmospheric or an elevated pressure of an inert gas, e.g. N2 and a solvent may optionally be used. Solvents specified are: n-hexane, ligroin, benzene, xylene, dioxane, diethylene glycol, diethyl ether, dimethyl formamide, dimethyl sulphoxide, N - acylmorpholines, N - methylpyrrolidone, N - ethyl - pyrrolidone, pyridine, picoline and tri-n-butylamine. The addition product may have 2-10 oxypropylene units per molecule and may contain up to 10% of polyoxypropylene glycol in admixture. In polyurethane production the polyols of the invention may be mixed with other polyols, e.g. linear polyethers, polyesters, aromatic polyethers, and sorbitol centred polyethers. Isocyanates specified are: ethylene diisocyanate, ethylidene diisocyanate, propylene-1,2 - diisocyanate, butylene - 1,2 - diisocyanate, hexylene - 1,6 - diisocyanate, cyclohexylene - 1, 2 - diisocyanate, m - phenylene diisocyanate, tolylene - 2,4 - diisocyanate, tolylene - 2,6 - diisocyanate, 3,31 - dimethyldiphenyl - 4, 41 - diisocyanate, 3,31 - dichlorodiphenyl - 4, 41 - diisocyanate, triphenylmethane - 4, 41,411 - triisocyanate, naphthalene-1, 4-diisocyanate reaction products of these with: hexane-1,2,6-triol, 1,1,1-trimethylolpropane, glycerol, propylene glycol, dipropylene glycol, tripropylene glycol, or mono-, di- or tri-ethylene glycol. Blowing agents specified are H2O, CCl2, F2, CCl3F and azo compounds The reaction may be a continuous process, a one-shot process or a prepolymer two-stage reaction. Other additives may be catalysts, e.g. N-methyl morpholine, triethylamine, N,N, N1, N1-tetra(2-hydroxypropyl) ethylene diamine, dibutyltin dilaurate, dibutyltin di(2-ethylhexoate), stannous octoate and stannous 2-ethylhexoate, foam stabilizers, e.g. polydimethylsiloxane, alkylsilane-polyoxyalkylene block copolymers, sorbitan monostearate and glycerol monooleate, pigments, fillers, e.g. glass fibre, nylon fibre, wool, polyvinyl chloride, mica, silica gel, alumina gel, asbestos and zinc oxide, antioxidants and stabilizers. The products may be rigid and of uniform cell size.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3049462 | 1962-07-17 | ||
JP3473262 | 1962-08-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB989144A true GB989144A (en) | 1965-04-14 |
Family
ID=26368856
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2781963A Expired GB989144A (en) | 1962-07-17 | 1963-07-12 | Polyether polyols and polyurethane foams derived therefrom |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE1545001A1 (en) |
GB (1) | GB989144A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110799561A (en) * | 2017-06-22 | 2020-02-14 | 株式会社三养社 | Composition for forming environmentally friendly polyurethane foam and method for producing polyurethane foam |
CN114222770A (en) * | 2019-07-12 | 2022-03-22 | 株式会社三养社 | Anhydrosugar alcohol-alkylene glycol composition, anhydrosugar alcohol-based urethane-modified polyol composition, and use thereof for epoxy resin composition |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102008011683A1 (en) * | 2008-02-28 | 2009-09-03 | Bayer Materialscience Ag | Process for the preparation of polyols |
-
1963
- 1963-07-12 GB GB2781963A patent/GB989144A/en not_active Expired
- 1963-07-16 DE DE19631545001 patent/DE1545001A1/en active Pending
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110799561A (en) * | 2017-06-22 | 2020-02-14 | 株式会社三养社 | Composition for forming environmentally friendly polyurethane foam and method for producing polyurethane foam |
EP3643732A4 (en) * | 2017-06-22 | 2021-03-24 | Samyang Corporation | Composition for forming environmentally friendly polyurethane foam and method for manufacturing polyurethane foam |
CN110799561B (en) * | 2017-06-22 | 2022-02-11 | 株式会社三养社 | Composition for forming environmentally friendly polyurethane foam and method for producing polyurethane foam |
EP3981815A1 (en) * | 2017-06-22 | 2022-04-13 | Samyang Corporation | Composition for forming environmentally friendly polyurethane foam and method for manufacturing polyurethane foam |
EP4321550A3 (en) * | 2017-06-22 | 2024-05-15 | Samyang Corporation | Composition for forming environmentally friendly polyurethane foam and method for manufacturing polyurethane foam |
CN114222770A (en) * | 2019-07-12 | 2022-03-22 | 株式会社三养社 | Anhydrosugar alcohol-alkylene glycol composition, anhydrosugar alcohol-based urethane-modified polyol composition, and use thereof for epoxy resin composition |
EP3998299A4 (en) * | 2019-07-12 | 2023-07-26 | Samyang Corporation | Anhydrous alcohol-alkylene glycol composition, anhydrous alcohol-based urethane-modified polyol composition, and uses of same for expoxy resin composition |
CN114222770B (en) * | 2019-07-12 | 2024-04-05 | 株式会社三养社 | Anhydrosugar alcohol-alkylene glycol composition, anhydrosugar alcohol-based urethane-modified polyol composition, and uses thereof |
Also Published As
Publication number | Publication date |
---|---|
DE1545001A1 (en) | 1969-07-24 |
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